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Updated: Nov 17, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Rapid Access to Diverse Potassium Acyltrifluoroborates (KATs) through Late-Stage Chemoselective Cross-Coupling
Xingwang Deng1, Guan Zhou1, Xiao Han1
1School of Pharmaceutical Science and Technology (SPST), Tianjin University, Building 24, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. China.
Abstract:
Potassium acyltrifluoroborates (KATs) are opening up new avenues in chemical biology, materials science, and synthetic organic chemistry due to their intriguing reactivities. However, the synthesis of these compounds remains mostly complicated and time-consuming. Herein, we have developed chemoselective Pd-catalyzed approaches for the late-stage diversification of arenes bearing prefunctionalized KATs. These approaches feature chemoselective cross-coupling, rapid diversification, functional group tolerance, mild reaction conditions, simple operation, and high yields.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

